These Chicago Bars Have Amazing Labor Day Specials

Sure, Labor Day is full of great events for your family and friends to enjoy, but you’re definitely going to need a few places to eat, too. And of course, you could just go to any restaurant that’s open, but why not take advantage of the various Labor Day specials happening at some of our favorite Chicago mainstays?

Show the relatives flying in from Jersey which city is really the best in the world (newsflash: NYC is not yours, Jersey), and take them to these Chicago restaurants with Labor Day specials.



Labor Day Trivia Night

Photo Credit: aliveOne Facebook

2683 N Halsted St


On Labor Day, aliveOne opens at 7 pm for a free music-themed trivia night, hosted by “Whaddayaknow?”, starting at 7:30 pm. With $4 to $8 drink specials for the whole night, aliveOne is the place to end up on Monday night.



Yoga on the Boat & End-Of-Season Party

Photo Credit: Castaways Facebook

1603 N Lake Shore Dr

From Saturday, September 1 through Monday, September 3, Castaways will be hosting guest DJs for their annual end-of-summer celebration. Plus, on Sunday from 9–10 am, you can participate in Yoga on the Boat alongside Yoga on the Beach for just $20, and that ticket even includes a mimosa or fresh-pressed juice. Cheers!



Notre Dame Season Opener Party & Labor Day Brunch

Photo Credit: Commonwealth Tavern Facebook

Commonwealth Tavern
2000 W Roscoe St


Saturday marks the beginning of the Notre Dame football season, so Commonwealth Tavern will be broadcasting their 2:30 pm game while you sip on their $5 20-ounce Miller Lite stadium cups, $5 Guinness, and $5 Jameson shots. Labor Day brunch will be served every day this weekend, including Monday, from 10 am–2 pm, so grab the whole family and head to Roscoe Village.



Labor Day Drink Specials

Easy Bar
Photo Credit: Easy Bar Facebook

Easy Bar
1944 W Division St

Open from 7 pm–2 am on Labor Day, this dog-friendly patio bar features specialty drinks, like their $8 “The Duffy”, $6 glasses of wine, $2 PBR, and $6 Tecate with a Jimador tequila shot.



Labor Day Food & Drink Specials

Photo Credit: Estelle’s Facebook

2013 W North Ave

With $3.50 to $8 food and drink specials after 11 pm on Monday evening, you can party all night long at Estelle’s. This casual bar is perfectly situated in the unassuming Wicker Park and supports a retro, diner-style atmosphere that feels just as cozy as it looks.


Happy Hour Kickoff to Labor Day Weekend & Bottomless Brunch

Hubbard Inn
Photo Credit: Hubbard Inn Facebook

Hubbard Inn
110 W Hubbard St

This bar starts Labor Day weekend as early as possible, with Happy Hour on Friday night from 4–7 pm. With bottomless brunch on Saturday and Sunday, you’ll be right back in the door the next day, chowing down on their chicken and waffles and other food specials from 10 am–3 pm. They are closed on Labor Day Monday.


Labor Day Rooftop Party & Happy Hour

Joy District
Photo Credit: Joy District Facebook

Joy District & Parlay
112 W Hubbard St

This rooftop bar is split into two sections: Joy District and Parlay. While Joy District will be hosting a rooftop party on Labor Day at 1 pm, you can slip downstairs to Parlay for Happy Hour from 4 pm–7 pm for even more drink specials. What a combo!


Weekend Drink Specials

Miller Lite Beer Garden
Photo Credit: Miller Lite Beer Garden Facebook

Miller Lite Beer Garden
700 E Grand

If you’re a Navy Pier-goer on holiday weekends like this, head to the Miller Lite Beer Garden for a weekend-long lineup of guest artists and DJs, as well as plenty of drink specials under $8 to hold you over.


Labor Day Weekend Happy Hour

Photo Credit: MAK Facebook

1924 W Division

Happy Hour starts on Friday through Monday from 5–7 pm, but make sure to stay extra long on Saturday night. From 5–9 pm, you can purchase half-price wine and sake at this Wicker Park restaurant.


Late Night Labor Day

Photo Credit: Remedy Facebook

1910 N Milwaukee Ave

Start your Labor Day night off right at Remedy, which will open at 6 pm for an unforgettable evening. Remedy features crafted drinks for under $8, so you can taste as many of their specialty cocktails as you want all night long.


Labor Day Weekend Brunch & Al Fresco Dining

Photo Credit: Roanoke Facebook

135 W Madison St

This Loop restaurant features a wide-open street patio, so you can enjoy Roanoke’s al fresco brunch out in the open Chicago air. Their weekend brunch is available from 10 am–3 pm on Saturday, Sunday, and Monday, so you have plenty of chances to indulge.


Labor Day Late Night Specials

The Owl
Photo Credit: The Owl Facebook

The Owl
2521 N Milwaukee Ave

The Owl is located off the beaten path from Milwaukee Avenue, so you’d miss it if you blinked. In fact, once you walk through the front doors, it might take a few blinks to get your eyes to adjust. But once you’re in, you’ll quickly get accustomed to the darkness and enjoy their $3 domestic macro beer specials until 4 am on Labor Day. What a way to celebrate!


About Author